Best and worst...

Worst: The girl was drunk. She basically clamped down on my cock and wanted me to fuck her mouth that way... Ouch.Her teeth left bruises all over my shaft. I managed to cum in her mouth, but I think it was more to spite her than because I enjoyed it.

The best was a time, I started a simple encounter with my SIL. We progressed through kissing, each of us doing some oral on the other. We we tried to do it, she said it hurt. I was almost begging. Finish me with your mouth. What started out as a pretty pedestrian "get it done" wound up with the most extended deep-throat I had ever imagined. When I came, it blew cum out of her nose. It was intense. Then she got worried about my brother finding out.

 

The worst. Was a girl who pretty much just sucked it like she was trying to get boulder through a straw. Basically clamped her mouth round it and went to town. Hard to describe the pain but jesus when I finally get her off I was purple and bruised. Brutal lol.

When I get the best ill let you know.

 

Worst.
I had a few bad ones, it's a little difficult to choose which one to choose.
One who scraped her teeth and hurt but turned to one of the best titfucks.
But I pick the one who kept reverting to her way after I told her a few times how to do it right. In the end I started going soft and I asked if I could use her breasts, it was obvious she was never going to be able to make me orgasm from her blowjob. She let me do and said to put it back in her mouth when I cum.
I started rubbing between her breasts and get hard soon after, and it didn't take long to reach orgasm. I edged twice with a very short interval in between and the third one came much sooner and stronger than I expected.
I told her I was cumming and put it back in her mouth - she was even ready with her mouth open to take me. I immediately started ejcaulating, she had this look on her face, took my cock out and I finished on her belly as it ejaculated without force.
She asked me to put it in her mouth, yet she complained when I did.


For the best I choose my fwb for a few reasons. She asked me to show her how to give blowjobs after saying she would never have a man in her mouth but one day she asked me to teach her and she ended up loving taking me. She also blew my mind how good she became.
Once she reached the point she was fine with making me cum in her mouth, that was the topping moment after discovering that my semen in her mouth was not gross and it didn’t taste bad. She kept giving her best each time, to the point she deepthroated me; she enjoyed doing it and it turned her on.
Watching her lips reach the base of my shaft was impressive, she truly tried to put more in, I could feel her push her lips against my body, she stayed down on it a good while.
She enjoyed holding the shaft and balls and made it feel amazing, I moaned lots.
After a good length of time she was getting a bit sore and asked me what she needed to do to finish me. She did exactly the way I desired, I always warned her when I was about to ejaculate. when I did, I could hear her breathe hard and fast with a little moan.
I found out later it was because she was very aroused, turned on.
So, she never stopped even after I was clearly not ejaculating anymore. She was very excited feeling my cock twitch in her mouth, feeling the cock swell, hearing my pleasure. At the beginning she was very self conscious and didn’t want me to watch. Now, she was also turned on knowing I was watching her, that seeing her do was beautiful and a turn on.
I had several blowjobs where I had to milk the last few drops out before, but with her, it was all drained out of my body. She never stopped until I told her she could stop.
And it was not because I was too sensitive, this was one rare woman who did it in a way I was able to enjoy receiving oral long past the ejaculation. Just amazing and impressive.
I stopped her just not to take advantage of her despite my fantasy of non stop oral until I cum again, or go soft.
She was so pleased with what she did for me and it made her more than ready to get her turn, giving me those blowjobs made her wet, throbbing and tingling.